Search for Cheap Deals on
Hotels in Winter Haven

Choose from 39380 Winter Haven Hotel Deals

Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL

2 out of 5
1300 3rd St Winter Haven FL
  • 7 min drive from LEGOLAND® Florida
Stay at this motel in Winter Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7/10 Good! (1,017 reviews)
Yes and yes

Reviewed on Feb 21, 2026

Howard Johnson by Wyndham Winter Haven FL
LEGOLAND Beach Retreat

LEGOLAND Beach Retreat

3 out of 5
100 Legoland Way SE Winter Haven FL
  • 11 min walk from LEGOLAND® Florida
Stay at this hotel in Winter Haven. Enjoy free breakfast, parking (surcharge), and a 24-hour front desk. Popular attractions LEGOLAND® Florida and Peppa Pig ...
9/10 Wonderful! (167 reviews)
Everything

Reviewed on Feb 12, 2026

LEGOLAND Beach Retreat
Legoland Florida Hotel

Legoland Florida Hotel

3 out of 5
1 Legoland Way Winter Haven FL
  • 1 min walk from LEGOLAND® Florida
Stay at this hotel in Winter Haven. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Popular attractions LEGOLAND® Florida and Peppa Pig Theme Park Florida ...
8.8/10 Excellent! (74 reviews)
This was our first visit to Legoland, and the kids loved it. The hotel is clean and well-maintained. It is clearly set up for kids with Lego everywhere. We went in February, and the hotel was very quiet, which was nice. The walk from the hotel to the theme park is less than 2 minutes.

Reviewed on Feb 16, 2026

Legoland Florida Hotel
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue Winter Garden FL
  • 1 hour drive from LEGOLAND® Florida
Book a stay at this family-friendly resort in Four Corners. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff ...
8/10 Very Good! (9,063 reviews)
Staff was great, amenities were amazing, such a relaxing stay, the room was so spacious. Just wish they could have kept their word and accommodated the late check out they mentioned for me at check in. But otherwise, it was great and will stay again.

Reviewed on Feb 19, 2026

The Grove Resort & Water Park Orlando
Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration

3 out of 5
2975 Arabian Nights Blvd Kissimmee FL
  • 1 hour drive from LEGOLAND® Florida
Book a stay at this family-friendly condo in Kissimmee. Enjoy free WiFi, 7 outdoor pools, and 7 hot tubs. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (3,404 reviews)
Really good for the price

Reviewed on Feb 20, 2026

Vacation Village Orlando, Celebration
Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

3 out of 5
7491 W Irlo Bronson Memorial Hwy Kissimmee FL
  • 1 hour drive from LEGOLAND® Florida
Stay at this resort in Kissimmee. Enjoy free WiFi, 2 hot tubs, and 2 outdoor pickleball courts. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN ...
9.4/10 Exceptional! (2,766 reviews)
Yes

Reviewed on Feb 19, 2026

Kompose Boutique Resort at Theme Parks
Holiday Inn Club Vacations at Orange Lake Resort by IHG

Holiday Inn Club Vacations at Orange Lake Resort by IHG

4 out of 5
8505 W Irlo Bronson Memorial Hwy Kissimmee FL
  • 1 hour drive from LEGOLAND® Florida
Book a stay at this golf resort in Kissimmee. Enjoy free WiFi, free parking, and 7 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
8.6/10 Excellent! (2,638 reviews)
Great resort

Reviewed on Feb 19, 2026

Holiday Inn Club Vacations at Orange Lake Resort by IHG
Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando

4 out of 5
7600 Mystic Dunes Lane Kissimmee FL
  • 57 min drive from LEGOLAND® Florida
Book a stay at this golf property in Kissimmee. Enjoy free WiFi, free parking, and 4 outdoor pools. Our guests praise the pool and the restaurant in our reviews. ...
9/10 Wonderful! (4,683 reviews)
Yes.

Reviewed on Feb 19, 2026

Hilton Vacation Club Mystic Dunes Orlando
Margaritaville Resort Orlando

Margaritaville Resort Orlando

4 out of 5
8000 Fins Up Circle Kissimmee FL
  • 1 hour drive from LEGOLAND® Florida
Book a stay at this spa resort in Kissimmee. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the restaurant in our reviews. ...
8.8/10 Excellent! (3,598 reviews)
Just excellent.

Reviewed on Feb 18, 2026

Margaritaville Resort Orlando
Ramada by Wyndham Kissimmee Gateway

Ramada by Wyndham Kissimmee Gateway

3 out of 5
7470 W. Irlo Bronson Memorial Hwy. Kissimmee FL
  • 59 min drive from LEGOLAND® Florida
Book a stay at this business-friendly hotel in Kissimmee. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff ...
8/10 Very Good! (3,926 reviews)
area

Reviewed on Feb 21, 2026

Ramada by Wyndham Kissimmee Gateway
Holiday Inn & Suites Orlando SW - Celebration Area by IHG

Holiday Inn & Suites Orlando SW - Celebration Area by IHG

3 out of 5
5711 W Irlo Bronson Memorial Hwy Kissimmee FL
  • 1 hour drive from LEGOLAND® Florida
Book a stay at this family-friendly hotel in Kissimmee. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.2/10 Very Good! (2,301 reviews)
The location was very good! We were very happy with the options for food and entertainment in the general area. The rooms could have been a little cleaner.

Reviewed on Feb 18, 2026

Holiday Inn & Suites Orlando SW - Celebration Area by IHG
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
7700 Westgate Blvd. Kissimmee FL
  • 58 min drive from LEGOLAND® Florida
Book a stay at this family-friendly resort in Kissimmee. Enjoy free WiFi, free parking, and 14 outdoor pools. Our guests praise the helpful staff and the clean ...
8/10 Very Good! (1,455 reviews)
All good

Reviewed on Feb 18, 2026

Westgate Town Center Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find cheap hotels in Winter Haven

You’re not an average traveler—and Hotwire knows it. Your wanderlust takes you off the beaten path to discover unique adventures and every travel destination’s lesser-known tourist scenes. Hotwire has the hookup! Book your Winter Haven hotel with Hotwire to complete your one-of-a-kind travel checklist.

For you, intrepid voyager, Hotwire has a large selection of the best hotels in Winter Haven.

Choosing the right hotel in Florida has everything to do with the way you want your trip to go. If you’ve scribbled a few obscure destinations on your itinerary, you probably already have a good sense of how your getaway is taking shape. Lean into that by booking one of Winter Haven’s 39,380 hotels. Choose the one that best catches your trip’s tourist drift.

If you’re traveling during the week for business, Hotwire can score you a luxury hotel for as low as $57. In town for pleasure? Hotwire still has you covered. If you’re in the mood for a quick last-minute weekend getaway or spa retreat, you can get great Winter Haven hotel deals at the last minute.

While traveling, where you stay plays a major role in your overall vacation enjoyment. Choosing the right hotel is just as important as making sure you book the right flight and car rental. If you’re traveling with family or friends, you may need to book a hotel with connecting rooms. If you enjoy an elegant and relaxing hotel ambiance, opt for one of Hotwire’s luxury hotels in Winter Haven. No matter your reason for visiting Winter Haven, with Hotwire’s large selection of hotels in the area, you’re sure to book a hotel that meets all your accommodation needs.

Frequently Asked Questions About Winter Haven hotels

Where can I find the best last-minute travel deals?

If you’re traveling in the spirit of spontaneity, you’ll love the idea of leaving your exact hotel choice up to chance. With Hotwire Hot Rates, you can unlock great deals on your next flight, hotel, or car rental. Just plug in your general preferences and let Hotwire choose last-minute hotel deals in Winter Haven for as low as $57.

How many hotels are there in Winter Haven?

With over 39,380 hotels in Winter Haven, you’re sure to find one that best matches your travel mood. When you book with Hotwire, you can score a stellar home away from home for as low as $57.

How to find cheap car rentals in Winter Haven?

Finding a cheap car rental deal in Winter Haven is as easy as scoring cheap hotels in Winter Haven. Hotwire partners with top-of-the-line car rental companies to bring you a large selection of affordable options. Whether you’re in need of a large SUV for the entire family or a more compact but stylish vehicle, Hotwire has you covered. You can unlock great car rental deals if you book a Hotwire Hot Rate at the last minute.